DE68913397T2 - Verwendung von 5-heteroaryl- oder 5-arylsubstituierten Imidazo(2,1-a)isochinolinen. - Google Patents

Verwendung von 5-heteroaryl- oder 5-arylsubstituierten Imidazo(2,1-a)isochinolinen.

Info

Publication number: DE68913397T2
Authority: DE; Germany
Prior art keywords: compound; pharmaceutical composition; pharmaceutically acceptable; group; dihydroimidazo
Prior art date: 1988-07-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

DE68913397T

Other languages

German (de)

English (en)

Other versions

DE68913397D1 (de

Inventor

William Joseph Houlihan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sandoz AG

Original Assignee

Sandoz AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-07-29

Filing date

1989-07-25

Publication date

1994-08-11

1989-07-25 Application filed by Sandoz AG filed Critical Sandoz AG

1994-04-07 Publication of DE68913397D1 publication Critical patent/DE68913397D1/de

1994-08-11 Application granted granted Critical

1994-08-11 Publication of DE68913397T2 publication Critical patent/DE68913397T2/de

2009-07-26 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

BYLPZVAKOZYZPH-UHFFFAOYSA-N imidazo[2,1-a]isoquinoline Chemical class C1=CC=C2C3=NC=CN3C=CC2=C1 BYLPZVAKOZYZPH-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 52
239000002253 acid Substances 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 10
208000006673 asthma Diseases 0.000 claims description 8
238000011321 prophylaxis Methods 0.000 claims description 8
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
FROPPKHARQXBNP-UHFFFAOYSA-N 5-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]phenyl]-2,3-dihydroimidazo[2,1-a]isoquinoline;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CCC=2C=CC(=CC=2)C=2N3CCN=C3C3=CC=CC=C3C=2)=C1 FROPPKHARQXBNP-UHFFFAOYSA-N 0.000 claims description 4
239000003380 propellant Substances 0.000 claims description 4
239000006199 nebulizer Substances 0.000 claims description 3
229940098458 powder spray Drugs 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000000080 wetting agent Substances 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
238000012360 testing method Methods 0.000 description 34
239000013566 allergen Substances 0.000 description 17
241001465754 Metazoa Species 0.000 description 15
239000000443 aerosol Substances 0.000 description 14
230000000694 effects Effects 0.000 description 8
210000003979 eosinophil Anatomy 0.000 description 8
108010058846 Ovalbumin Proteins 0.000 description 7
229940092253 ovalbumin Drugs 0.000 description 7
210000004027 cell Anatomy 0.000 description 6
239000000243 solution Substances 0.000 description 5
239000003814 drug Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
210000004072 lung Anatomy 0.000 description 4
230000009257 reactivity Effects 0.000 description 4
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 3
SKDFWEPBABSFMG-UHFFFAOYSA-N 1,2-dichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)CCl SKDFWEPBABSFMG-UHFFFAOYSA-N 0.000 description 3
241000700199 Cavia porcellus Species 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
238000009825 accumulation Methods 0.000 description 3
229940109248 cromoglycate Drugs 0.000 description 3
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
238000011597 hartley guinea pig Methods 0.000 description 3
238000000034 method Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
241000700198 Cavia Species 0.000 description 2
-1 Cromoglycate Compound Chemical class 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
VLBPIWYTPAXCFJ-XMMPIXPASA-O Lyso-PAF C-16-d4 Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](O)COP(O)(=O)OCC[N+](C)(C)C VLBPIWYTPAXCFJ-XMMPIXPASA-O 0.000 description 2
108700020675 O-deacetyl platelet activating factor Proteins 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000000692 Student's t-test Methods 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000036428 airway hyperreactivity Effects 0.000 description 2
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 2
239000002158 endotoxin Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
210000000265 leukocyte Anatomy 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
WCYWCJPGHHIEMQ-UHFFFAOYSA-N 5-[3-[(3,4,5-trimethoxyphenyl)methoxy]phenyl]-2,3-dihydroimidazo[2,1-a]isoquinoline;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(COC=2C=C(C=CC=2)C=2N3CCN=C3C3=CC=CC=C3C=2)=C1 WCYWCJPGHHIEMQ-UHFFFAOYSA-N 0.000 description 1
ORMMPTNCDLUQTP-UHFFFAOYSA-N 5-[3-[2-(3,4,5-trimethoxyphenyl)ethyl]phenyl]-2,3-dihydroimidazo[2,1-a]isoquinoline;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CCC=2C=C(C=CC=2)C=2N3CCN=C3C3=CC=CC=C3C=2)=C1 ORMMPTNCDLUQTP-UHFFFAOYSA-N 0.000 description 1
PQIXUJAMYUOYCA-UHFFFAOYSA-N 5-[4-[(2,3,4-trimethoxyphenyl)methoxy]phenyl]-2,3-dihydroimidazo[2,1-a]isoquinoline;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC=C1COC1=CC=C(C=2N3CCN=C3C3=CC=CC=C3C=2)C=C1 PQIXUJAMYUOYCA-UHFFFAOYSA-N 0.000 description 1
IOECDNMYMZTIKX-UHFFFAOYSA-N 5-[4-[(3,4,5-trimethoxyphenyl)methoxy]phenyl]-2,3-dihydroimidazo[2,1-a]isoquinoline;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(COC=2C=CC(=CC=2)C=2N3CCN=C3C3=CC=CC=C3C=2)=C1 IOECDNMYMZTIKX-UHFFFAOYSA-N 0.000 description 1
WESFDWYPTKSKGP-UHFFFAOYSA-N 5-[4-[6-(3,4,5-trimethoxyphenyl)hexyl]phenyl]-2,3-dihydroimidazo[2,1-a]isoquinoline;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CCCCCCC=2C=CC(=CC=2)C=2N3CCN=C3C3=CC=CC=C3C=2)=C1 WESFDWYPTKSKGP-UHFFFAOYSA-N 0.000 description 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
206010014950 Eosinophilia Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
229920005372 Plexiglas® Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
229940125717 barbiturate Drugs 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
229960003957 dexamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
238000002513 implantation Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
231100000516 lung damage Toxicity 0.000 description 1
239000012528 membrane Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000003305 oral gavage Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
229960004618 prednisone Drugs 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
201000009732 pulmonary eosinophilia Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
231100000057 systemic toxicity Toxicity 0.000 description 1
238000010998 test method Methods 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
238000011282 treatment Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DE68913397T 1988-07-29 1989-07-25 Verwendung von 5-heteroaryl- oder 5-arylsubstituierten Imidazo(2,1-a)isochinolinen. Expired - Fee Related DE68913397T2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US22630588A	1988-07-29	1988-07-29
US07/302,720 US4910206A (en)	1986-07-14	1989-01-27	5-hetero-or aryl-substituted-imidazo(2,1-a)isoquinolines and their use as PAF receptor antagonists

Publications (2)

Publication Number	Publication Date
DE68913397D1 DE68913397D1 (de)	1994-04-07
DE68913397T2 true DE68913397T2 (de)	1994-08-11

Family

ID=26920416

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE68913397T Expired - Fee Related DE68913397T2 (de)	1988-07-29	1989-07-25	Verwendung von 5-heteroaryl- oder 5-arylsubstituierten Imidazo(2,1-a)isochinolinen.

Country Status (16)

Country	Link
US (1)	US4910206A (pt)
EP (1)	EP0357550B1 (pt)
JP (1)	JPH0273016A (pt)
KR (1)	KR910002445A (pt)
AU (1)	AU632487B2 (pt)
CA (1)	CA1336503C (pt)
DE (1)	DE68913397T2 (pt)
DK (1)	DK372089A (pt)
ES (1)	ES2062092T3 (pt)
FI (1)	FI893616A (pt)
HU (1)	HU206040B (pt)
IE (1)	IE63243B1 (pt)
IL (1)	IL91128A (pt)
NO (1)	NO177485C (pt)
NZ (1)	NZ230098A (pt)
PT (1)	PT91302B (pt)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0345931B1 (en) *	1988-04-27	1993-01-20	Schering Corporation	Certain paf antagonist/antihistamine combinations and methods
US5530141A (en) *	1992-03-04	1996-06-25	Center For Innovative Technology	2,4-diaryl-1,3-dithiolanes; 2,4-diaryl-1,3-dioxolanes; 2,4-diaryl-1,3-oxathiolanes; and 2,5-diaryl-1,3-oxathiolanes for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
US5639782A (en) *	1992-03-04	1997-06-17	Center For Innovative Technology	Neolignan derivatives as platelet activating factor receptor antagonists and 5-lipoxygenase inhibitors
US5358938A (en) *	1992-07-13	1994-10-25	Cytomed, Inc.	Compounds and methods for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
US5434151A (en) *	1992-08-24	1995-07-18	Cytomed, Inc.	Compounds and methods for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
CA2140034A1 (en)	1992-07-13	1994-01-20	Xiong Cai	2,5-diaryl tetrahydro-thiophenes, -furans and analogs for the treatment of inflammatory and immune disorders
US5648486A (en) *	1992-07-13	1997-07-15	Cytomed, Inc.	Compounds and methods for the treatment of inflammatory and immune disorders
US5463083A (en) *	1992-07-13	1995-10-31	Cytomed, Inc.	Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5792776A (en) *	1994-06-27	1998-08-11	Cytomed, Inc.,	Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5750565A (en) *	1995-05-25	1998-05-12	Cytomed, Inc.	Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5703093A (en) *	1995-05-31	1997-12-30	Cytomed, Inc.	Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
FR2756560A1 (fr) *	1996-12-04	1998-06-05	Adir	Nouveaux derives de l'imidazoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CN1076728C (zh) *	1999-02-05	2001-12-26	浙江大学	2－芳基咪唑并[2,1－a]异喹啉的衍生物及其用途
CN112574176B (zh) *	2019-09-27	2024-03-15	隆泰申医药科技(南京)有限公司	一种杂芳基类化合物及其应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4101553A (en) *	1974-01-02	1978-07-18	Sandoz, Inc.	Imidazo[2,1-a]isoquinolines
HU172649B (hu) *	1975-04-24	1978-11-28	Gyogyszerkutato Intezet	Sposob poluchenija novykh biologicheski aktivnykh lizergamidov
EP0258175B1 (en) *	1986-07-14	1992-04-01	Sandoz Ag	5-hetero- or aryl-substituted-imidazo[2,1-a]isoquinolines

1989
- 1989-01-27 US US07/302,720 patent/US4910206A/en not_active Expired - Fee Related
- 1989-07-18 HU HU893613A patent/HU206040B/hu not_active IP Right Cessation
- 1989-07-25 DE DE68913397T patent/DE68913397T2/de not_active Expired - Fee Related
- 1989-07-25 EP EP89810565A patent/EP0357550B1/en not_active Expired - Lifetime
- 1989-07-25 ES ES89810565T patent/ES2062092T3/es not_active Expired - Lifetime
- 1989-07-27 NO NO893062A patent/NO177485C/no unknown
- 1989-07-27 PT PT91302A patent/PT91302B/pt not_active IP Right Cessation
- 1989-07-27 IL IL9112889A patent/IL91128A/en not_active IP Right Cessation
- 1989-07-27 NZ NZ230098A patent/NZ230098A/en unknown
- 1989-07-27 AU AU39017/89A patent/AU632487B2/en not_active Ceased
- 1989-07-27 DK DK372089A patent/DK372089A/da not_active Application Discontinuation
- 1989-07-28 JP JP1194436A patent/JPH0273016A/ja active Pending
- 1989-07-28 KR KR1019890010692A patent/KR910002445A/ko not_active Application Discontinuation
- 1989-07-28 FI FI893616A patent/FI893616A/fi not_active Application Discontinuation
- 1989-07-28 CA CA000606986A patent/CA1336503C/en not_active Expired - Fee Related
- 1989-07-28 IE IE245989A patent/IE63243B1/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK372089A (da)	1990-01-30
CA1336503C (en)	1995-08-01
FI893616A (fi)	1990-01-30
NO177485B (no)	1995-06-19
EP0357550A2 (en)	1990-03-07
PT91302A (pt)	1990-02-08
IE63243B1 (en)	1995-04-05
NZ230098A (en)	1992-02-25
NO177485C (no)	1995-09-27
DE68913397D1 (de)	1994-04-07
US4910206A (en)	1990-03-20
FI893616A0 (fi)	1989-07-28
EP0357550B1 (en)	1994-03-02
DK372089D0 (da)	1989-07-27
EP0357550A3 (en)	1991-04-03
NO893062L (no)	1990-01-30
JPH0273016A (ja)	1990-03-13
ES2062092T3 (es)	1994-12-16
PT91302B (pt)	1995-03-01
KR910002445A (ko)	1991-02-25
IL91128A (en)	1996-01-31
NO893062D0 (no)	1989-07-27
HU206040B (en)	1992-08-28
HUT50630A (en)	1990-03-28
AU632487B2 (en)	1993-01-07
AU3901789A (en)	1990-02-01
IL91128A0 (en)	1990-03-19
IE892459L (en)	1990-01-29

Legal Events

Date	Code	Title	Description
1995-03-30	8364	No opposition during term of opposition
1999-09-09	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
DE60026855T2 (de)	2006-12-07	Synergistische kombination von roflumilast und salmeterol
DE68913397T2 (de)	1994-08-11	Verwendung von 5-heteroaryl- oder 5-arylsubstituierten Imidazo(2,1-a)isochinolinen.
DE69918222T2 (de)	2005-07-28	Intranasale Zubereitungen zur Behandlung sexueller Störungen
EP1178832B1 (de)	2003-07-30	Neuartige arzneimittelkompositionen auf der basis von tiotropiumbromid und salmeterol
DE69736083T2 (de)	2006-12-28	Hochdosierte liposomale Aerosolformulierung
EP1121112B1 (de)	2002-06-05	Lagerfähiges wirkstoffkonzentrat mit formoterol
EP1526870B1 (de)	2007-05-02	Kombination von loteprednoletabonat und dfho zur behandlung von atemwegserkrankungen, allergischen erkrankungen, asthma und copd
DE2800954A1 (de)	1978-07-20	Derivate des meta-trifluoromethylphenylpiperazins und deren verwendung als arzneimittel
DE68904462T2 (de)	1993-05-13	4-chinolincarbonsaeure-derivate, brauchbar zur behandlung von haut- und muco-epithelial-gewebekrankheiten.
US4606920A (en)	1986-08-19	Pharmaceutical composition suitable for treatment of inflammatory changes of the bronchial mucosa
US5599817A (en)	1997-02-04	Xanthine derivatives as diuretic agents
CH634574A5 (de)	1983-02-15	Verfahren zur herstellung von 7-(2,3-dihydroxypropyl)-1,3-di-n-propylxanthin.
DE69125204T2 (de)	1997-06-26	Therapeutische Anwendung von Histamin-H3-Agonisten, neue Wirkstoffe und Verwendung zur Herstellung von Arzneimitteln
AT397097B (de)	1994-01-25	Neue alkoxyderivate der ginkgolide, ihre herstellung und sie enthaltende therapeutische zusammensetzungen
EP0821960B1 (de)	2003-04-09	Verwendung von Xanthinderivaten in Kombination mit einem 5-Isoxazol-4-carbonsäureamid Derivat und/oder einem 2-Cyano-3-hydroxy-crotonsäureamid Derivat zur Modulation der Apoptose
DE3852717T2 (de)	1995-05-18	Zusammensetzung für die Prophylaxe von Pneumocystis-carinii-Pneumonie.
DE2605243A1 (de)	1976-09-02	Pyrazolessigsaeurehaltiges arzneimittel
DE2932402C2 (pt)	1988-12-22
WO1983003758A1 (en)	1983-11-10	Pharmaceutical composition having a cystostatic activity
DE3544457A1 (de)	1987-06-19	Arzneimittel zur behandlung von leberkrankheiten
DE2737735C3 (de)	1979-10-25	Pirbutero\ und Hydroxyzin enthaltende Arzneimittel
DE2704774C3 (de)	1984-09-20	Bronchodilatator
AT380251B (de)	1986-05-12	Verfahren zur herstellung von neuen cycloalkyltriazolen und deren salzen
CH653555A5 (de)	1986-01-15	Eine nasal verabreichbare pharmazeutische zusammensetzung.
DE4236917A1 (de)	1994-05-05	Verwendung von 8-(3-Oxocyclopentyl)-1,3-dipropyl-7H-purin-2,6-dion zur Behandlung von Lungenerkrankungen